Synthesis, surface properties of glucosyl esters from renewable materials for use as biosurfactants

An, Dong; Zhang, Xianlong; Liang, Fengbing; Xian, Ming; Feng, Dexin; Z, Ye

doi:10.1016/j.colsurfa.2019.05.079

Cited by 22 publications

(36 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, the authors estimated that 8–10% of the Novozym 435 activity was lost per cycle at the end of the reuse. In another study, the conversion of glucose esters from different N-fatty acyl glycines decreased 30% for the 5th 9 h cycle with Novozym 435 [ 73 ].…”

Section: Resultsmentioning

confidence: 99%

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

et al. 2021

View full text Add to dashboard Cite

In this paper, we have performed the Lipozyme 435-catalyzed synthesis of xylose oleate in methyl ethyl ketone (MEK) from xylose and oleic acid. The effects of substrates’ molar ratios, reaction temperature, reaction time on esterification rates, and Lipozyme 435 reuse were studied. Results showed that an excess of oleic acid (xylose: oleic acid molar ratio of 1:5) significantly favored the reaction, yielding 98% of xylose conversion and 31% oleic acid conversion after 24 h-reaction (mainly to xylose mono- and dioleate, as confirmed by mass spectrometry). The highest Lipozyme 435 activities occurred between 55 and 70 °C. The predicted Ping Pong Bi Bi kinetic model fitted very well to the experimental data and there was no evidence of inhibitions in the range assessed. The reaction product was purified and presented an emulsion capacity close to that of a commercial sugar ester detergent. Finally, the repeated use of Lipozyme 435 showed a reduction in the reaction yields (by 48 and 19% in the xylose and oleic acid conversions, respectively), after ten 12 h-cycles.

show abstract

Section: Resultsmentioning

confidence: 99%

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Our study began by utilizing our previously optimal catalytic system of (COD)Pd(CH 2 SiMe 3 ) 2 ( 2 ) and tris (2,2,2‐trifluoroethyl)phosphite, and we were delighted to observe the desired cyclization of 3 in reasonable yield (Table , entry 1). We recognized, however, that 2 has limited commercial availability and is somewhat thermally sensitive . As such, we investigated the use of more accessible palladium precatalysts.…”

Section: Figurementioning

confidence: 79%

“…Finally, we have found that the catalytic conditions developed for this aza‐Heck cyclization also work with cyclizations of O ‐phenyl hydroxamates. Compared to our previously published reaction conditions, which required the use of thermally sensitive 2 , the yields using these new conditions are either comparable or higher with much lower catalyst loading (Scheme ). More importantly, these new conditions only require widely available precatalyst components, which considerably lowers the barrier for application of this method.…”

Section: Figurementioning

confidence: 99%

Synthesis of N−H Bearing Imidazolidinones and Dihydroimidazolones Using Aza‐Heck Cyclizations

Shuler

Watson

2018

Angew Chem Int Ed

View full text Add to dashboard Cite

The synthesis of unsaturated, unprotected imidazolidinones via an aza-Heck reaction is described. This palladium-catalyzed process allows for the cyclization of N-phenoxy ureas onto pendant alkenes. The reaction has broad functional group tolerance, can be applied to complex ring topologies, and can be used to directly prepare mono- and bis-unprotected imidazolidinones. By addition of Bu NI, dihydroimidazolones can be accessed from the same starting materials. Improved conditions for preparing unsaturated, unprotected lactams are also reported.

show abstract

“…Pd(II) OACs have been further utilised in pharmaceutical diversification, [21,22] and whilst their utility cannot be overstated, their adoption has been limited by unstable precursors [23] . Whilst the OACs themselves are often air and moisture stable, their formation requires the use of (1,5‐cyclooctadiene)Pd(II)(CH 2 TMS) 2, [24] or Pd(0)(1,5‐cyclooctadiene) ligated with a phosphine ligand [25] . Both of these precursors require manipulation in a glovebox.…”

Section: Figurementioning

confidence: 99%

Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation

Frost

Tilden

Lubben

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition‐metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C−H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user‐friendly synthesis, common Pd(II) sources, and a more cost‐effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility.

show abstract

Synthesis, surface properties of glucosyl esters from renewable materials for use as biosurfactants

Cited by 22 publications

References 25 publications

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

Synthesis of N−H Bearing Imidazolidinones and Dihydroimidazolones Using Aza‐Heck Cyclizations

Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation

Contact Info

Product

Resources

About